RX J0806.3+1527 is a candidate double degenerate binary with possibly the shortest known orbital period. The source shows an approximately equal to 100% X-ray intensity modulation at the putative orbital frequency of 3.11 mHz (321.5 s). If the system is a detached, ultracompact binary gravitational radiation should drive spin-up with a magnitude of nu(sup dot) approximately 10(exp -16) Hz per second. Efforts to constrain the X-ray frequency evolution to date have met with mixed success, principally due to the sparseness of earlier observations. Here we describe the results of the first phase coherent X-ray monitoring campaign on RX J0806.3+1527 with Chandra. We obtained a total of 70 ksec of exposure in 6 epochs logarithmically spaced over 320 days. With these data we conclusively show that the X-ray frequency is increasing at a rate of 3.77 plus or minus 0.8 x 10(exp -16) Hz per second. Using the ephemeris derived from the new data we are able to phase up all the earlier Chandra and ROSAT data and show they are consistent with a constant nu(sup dot) = 3.63 plus or minus 0.06 x 10(exp -16) Hz per second over the past decade. This value appears consistent with that recently derived by Israel et al. largely from monitoring of the optical modulation, and is in rough agreement with the solutions reported initially by Hakala et al., based on ground-based optical observations. The large and stable nu(sup dot) over a decade is consistent with gravitational radiation losses driving the evolution. An intermediate polar (IP) scenario where the observed X-ray period is the spin period of an accreting white dwarf appears less tenable because the observed nu(sup dot) requires an m(sup dot) approximately equal to 4 x 10 (exp -8) solar mass yr(sup -l), that is much larger than that inferred from the observed X-ray luminosity (although this depends on the uncertain distance and bolometric corrections), and it is difficult to drive such a high m(sup dot) in a binary system with parameters consistent with all the multiwavelength data. If the ultracompact scenario is correct, then the X-ray flux cannot be powered by stable accretion which would drive the components apart, suggesting a new type of energy source (perhaps electromagnetic) may power the X-ray flux.